He plays with the sensitive skin areas around her breasts until she's suitably worked up, before his hand goes slipping down towards her jeans and panties again, this time slipping them completely down under her ass to her mid thigh, a little easier than it probably should be in this position. The fingers traceback over the curve of her ass and her hip before one finds it's way between to gibe a small stroke. Again he's testing, finding her limits and her likes, lacking the caution to be tentatively up also not so boldly as to be overpowering. He really wasn't joking when he made the comment about making sure his partners were well looked after in that way, and in this case leafing a little bit as she seems to be not yet confident enough to just take what she wants in the way that he likes the most. He has no doubts that they may get there eventually, but until then he's gonna focus in on making sure she's pleased.